


Keeping Insecurities Under Clothes

by orphan_account



Category: Teen Wolf (TV)
Genre: Crossdressing Kink, Enemies to Lovers, Feminization, Hand Jobs, Humiliation, Kink Discovery, Lingerie, M/M, Underwear Kink, Women's Underwear
Language: English
Status: Completed
Published: 2016-04-15
Updated: 2016-04-15
Packaged: 2018-06-02 10:24:34
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,042
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6562642
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Stiles makes the mistake of leaving his locker open. Jackson decides to take advantage of it.</p>
            </blockquote>





	Keeping Insecurities Under Clothes

**Author's Note:**

> Un-beta'd as hell. I have no idea what this is. I had a plot idea and had no idea how to write it because I'm probably the least kinky person ever so yeah, have a thing. I hope it isn't too terrible. I also had no idea how to tag this so I just sort of tagged everything.

There were times Stiles wished he could be just like every average straight boy he went to high school with and this definitely qualified as one of those times. Maybe if he wasn’t such an insecure and scrawny guy he wouldn’t feel so embarrassed about showering with the rest of the lacrosse team and wouldn’t purposely delay himself so he only showered after most of them had already taken off home. Add his newfound bisexuality on top of it and yeah, the locker room was pretty much a death trap for him. If he’d just been a bit more confident in his body ( _ha, fat chance_ ) and capable of stopping his eyes from wandering to other guy’s junk ( _again, not happening_ ) then maybe he wouldn’t have showered late and left Jackson Whittemore with unrestricted access to everything in his open locker.

Jackson had bullied Stiles for as long as he could really remember and Stiles had quickly developed thicker skin to put up with it. He learned quickly that Jackson only ran his mouth so often because he was just as insecure as Stiles was, except he had the good genes and money to back it up. Stiles only had his sarcasm as a defence and as great as that was against people like Jackson it really didn’t do much to help when he stared in the mirror and pointed out all the places you could see bone or where his body was freckled with moles. He resentfully imagined how flawless Jackson’s body was and how _unfair_ this whole “gene lottery” thing was. It wasn’t like Stiles thought his parents had bad genes, he’d just not seemed to get many of the good ones. Would it really have whatever higher power or science there was to make him a bit taller and a bit more handsome?

Things with Jackson had changed over the last month though and Stiles was still struggling to get used to it. He’d always been curious about why Jackson was such good friends with Danny and even though he didn’t want to be presumptuous, he presumed that they’d at least fooled around and Jackson was maybe a little bi-curious. That had turned out to be a pretty correct guess given the fact that just a few weeks ago Jackson had invited Stiles to jerk him off and he’d actually done it. The experience had been kind of awkward and a little uncomfortable for the both of them but that hadn’t stopped Jackson for cornering him at his locker a few days later and demanding a blowjob after practice that day.

Stiles supposed he should have been ashamed with the fact he actually went through with it. He couldn’t help it! It was all because of Jackson and his stupidly pretty face.

The little “favors” he’d been doing Jackson hadn’t stopped the guy from being the biggest douchebag to ever walk the halls of Beacon Hills High School but Stiles hadn’t really expected that either. It was as if being a jerk was something Jackson needed to survive, like some sort of social vampire. He’d still push Stiles into lockers and snark about how he was never going to see any playtime during the lacrosse season (which, to be fair, was probably true) but then he’d turn around and demand that Stiles blow him and every time he’d go along with it. Jackson had a really nice cock and it wasn’t as if Stiles was getting any action elsewhere after all.

Only this time, Jackson took things a bit further and Stiles wasn’t sure if he was supposed to be horrified or aroused. Maybe it was a bit of both because as he walked out of the showers with a towel around his waist, he discovered the jock stood by his empty locker with Stiles’ pants in one hand and a pair of pink lace panties in the other. Stiles felt his stomach drop and he was pretty sure his skin became so pale he might as well have become a ghost.

“What the hell did you do?” he muttered, unable to take his eyes off the lingerie in Jackson’s hand. He already had a horrible feeling he knew exactly what they were for.

Jackson was wearing that smug grin on his face that made Stiles’ blood boil but also made his cock twitch and he wished for about the hundredth time that it wasn’t _Jackson_ that had that kind of effect on him. Why couldn’t it have been somebody nice like Danny or god, even Scott? Hell, he’d even take Greenberg over Jackson. Things would be so much simpler that way but no, his body had to go and be attracted to the biggest douche Stiles had ever met. _Way to be a traitor, body._

“Just did a little cleaning for you. Threw out those boxers of yours since you clearly know nothing about hygiene,” Jackson rattled off, savouring every word and every twitch of Stiles’ face. “Thought I’d give you a present.”

“I don’t want any presents from you,” Stiles growled in response. Jackson’s grin only got wider.

“If you wanna leave here with any pants on at all then you’ll want the present,” he fired back without missing a beat. As if to prove his point he moved Stiles’ pants further away and the skinnier teen realized in misery just how serious the other was. “Make your choice, Stilinski.”

Stiles narrowed his eyes at the lingerie being offered to him. It was just so _pink_ and feminine, nothing like what he would choose to wear… and yet the thought actually excited him. He really didn’t want to consider why his brain had decided to work like that. The fact his cock seemed to agree only made things so much worse and he realized miserably that his towel had started to tent. It certainly hadn’t escaped Jackson’s attention either.

“Well?”

“Give them here,” Stiles muttered, snatching the panties out of Jackson’s hands. He tried to turn away and save himself some decency but the other boy grabbed him by the arm and spun him back around before shaking his head. Apparently forcing Stiles to wear women’s underwear wasn’t enough humiliation.

Dropping the towel, Stiles tried not to think about the way Jackson was looking at his half-hard cock and instead focused on pulling the panties up over his legs. The material was soft and pleasant against his skin - probably expensive, knowing Jackson - but it was unusually tented thanks to Stiles’ cock. He half expected Jackson to have his cell phone out to film his humiliation but instead the other boy was staring at him so intently that Stiles felt himself shiver. He didn’t think anybody had ever looked at him like he was a piece of meat before. “Did… did you buy these just for me?” he asked, purely to break through the silence that had grown between them. Jackson’s eyes wandered up to meet his gaze and a playful smirk appeared on his lips.

“Maybe,” he shrugged before stepping in closer until Stiles could feel Jackson’s breath against his cheek. “Or maybe they’re mine.” _Fuck_ , why did that thought turn him on so much? He was pretty sure his cock was about to break through the panties because the thought of Jackson dressed in them had sent Stiles’ brain into overdrive. _Holy shit, I did not realize I had this kink_. It was a realization and a half, one he was still struggling to accept when Jackson’s hand found its way to his cock and started to stroke it through the lacy material. Stiles couldn’t help but whimper. “You make such a pretty girl, Stilinski.”

Giving Jackson any power over him whatsoever was a big mistake and Stiles knew it but he couldn’t help how his body liked to be touched and what his brain liked to hear. He wasn’t sure _why_ his brain liked that but he was choosing not to focus on that right now. Well, he didn’t have much of a choice on the matter because pretty much every part of his brain was screaming about how good it felt to have Jackson touch him. He’d never had anybody touch him like this before and he was beyond overwhelmed at the sensations spreading throughout his body.

“You’re an ass,” he hissed as Jackson moved his hand under the material to get a better grip of Stiles’ cock and started to kiss at his overly-sensitive neck. In response the jock alternated between kissing, biting and sucking at the tender skin and it was sure to leave a mark eventually. _Oh god, how am I going to explain this to Scott? Or my dad? Fuck, you’re such an asshole, Whittemore._ This day really wasn’t going how Stiles had planned but all in all, he figured that maybe it was going a little better than he’d expected. At least he was getting an orgasm out of it, after all. It was the first time it had happened too because Jackson had always shied away from touching him, he was selfish and expected Stiles to do all the work most of the time. Stiles wasn’t sure what had happened to change that but he didn’t have it in him to complain either.

“Cum for me, baby,” Jackson whispered, sending Stiles straight to his climax. He let out a rather undignified cry and dropped his head down against Jackson’s shoulder, gasping desperately as he covered Jackson’s hands and the panties in his release. “Such a good girl,” Jackson whispered into his ear, finally removing his hand from Stiles’ junk and bringing his finger to his lips. Stiles lifted his head to watch as Jackson ran his tongue along the finger before taking it in his mouth. He hated how erotic the sight was and just how badly he was at resisting the desire he felt. “You taste so good,” the other enthused, looking as smug as ever. Stiles felt himself blush against better judgment.

“Can I have my pants now?” he asked finally. They had fallen from Jackson’s hands a few minutes earlier and laid abandoned on the locker room floor. Suddenly Stiles felt a desperate need to have them on and hide his shame from the other. He was just glad there was nobody else around to see him like this or he’d never live it down.

After a moment, Jackson stepped back out of Stiles’ personal space and grabbed the discarded pants. Stiles tried not to think about how his body mourned Jackson’s presence and instead accepted the pants as they were offered to him without ever meeting the other boy’s eyes. His insecurities about his body were starting to rush back, especially considering Jackson had remained clothed throughout the entire encounter while he had been utterly exposed.

“Keep the present,” Jackson said after a moment, dragging Stiles’ attention away from buckling his belt up properly. “It looks good on you, baby.” There it was again with the cocky look on Jackson’s face and the shiver down Stiles’ spine. He was pretty sure the other boy was going to be the death of him one way or the other.

“Yeah, whatever. I still hate you,” Stiles fired back, scowling as he watched Jackson’s perfect ass retreating towards the locker room door.

Despite better judgment, the panties somehow found their way into his regular underwear rotation among the baggy boxers that didn’t seem quite as comfortable in comparison. Stiles couldn’t help but feel special and perhaps even a little _sexy_ whenever he wore them and Jackson’s face always lit up with a smile when he caught sight of them poking out over Stiles’ waistband. It was a nightmare hiding them from his father and the other boys on the lacrosse team but somehow Stiles made it work. He actually liked having a dirty little secret that was just his and Jackson’s to share which was something he honestly never thought he’d say.

There was only one thing that had been bugging him since that afternoon in the locker room though: he had a desperate need to see Jackson in lingerie too. Maybe it was time he returned the favour and bought Jackson a present of his own…


End file.
